Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
9(3), С. 703 - 708
Опубликована: Дек. 10, 2021
Chiral
Lewis
acid-catalyzed
enantioselective
nitrooxylation
and
azidation
of
cyclic
acyclic
β-keto
amides/esters
with
hypervalent
iodine(
iii
)
reagents.
Chemical Communications,
Год журнала:
2023,
Номер
59(50), С. 7831 - 7834
Опубликована: Янв. 1, 2023
Copper-catalyzed
asymmetric
dearomative
azidation
of
tryptamines
using
azidobenziodoxolone
as
an
azidating
reagent
was
developed,
which
affords
a
variety
3a-azido-pyrroloindolines
in
good
to
high
enantioselectivities
under
mild
reaction
conditions.
The
azides
could
be
readily
transformed
into
the
corresponding
3a-amino-pyrroloindolines
via
reduction
and
1,2,3-triazole
derivatives
click
reaction.
Empowered
by
the
ubiquity
of
carbonyl
functional
groups
in
organic
compounds,
decarbonylative
functionalization
was
prevalent
construction
complex
molecules.
Under
this
context,
asymmetric
has
emerged
as
an
efficient
pathway
to
accessing
chiral
motifs.
However,
ablation
enantiomeric
control
a
conventional
2e
transition
metal–catalyzed
process
notable
because
harsh
conditions
(high
temperatures,
etc.)
that
are
usually
required.
To
address
challenge
and
use
readily
accessible
aldehyde
directly,
we
report
radical
azidation
cyanation.
Diverse
aldehydes
were
directly
used
alkyl
precursor,
engaging
subsequent
inner-sphere
or
outer-sphere
ligand
transfer
where
motifs
(CN
N
3
)
could
be
incorporated
excellent
site-
enantioselectivity.
Mild
conditions,
broad
scope,
regioselectivity
(driven
polarity-matching
strategy),
enantioselectivity
shown
for
both
transformations.
This
strategy
using
precursor
offered
powerful
reaction
manifold
transformations
construct
regio-
stereoselectively.
Angewandte Chemie,
Год журнала:
2020,
Номер
132(39), С. 17392 - 17397
Опубликована: Июнь 10, 2020
Abstract
The
first
Pd‐catalyzed
enantioselective
azidation
of
unactivated
alkenes
has
been
established
by
using
readily
accessible
1‐azido‐1,2‐benziodoxol‐3(1
H
)‐one
(ABX)
as
an
azidating
reagent,
which
affords
a
wide
variety
structurally
diverse
3‐N
3
‐substituted
piperidines
in
good
yields
with
excellent
enantioselectivity.
reaction
features
functional‐group
compatibility
and
mild
conditions.
Notably,
both
electrophilic
reagent
the
sterically
bulky
chiral
pyridinyl‐oxazoline
(Pyox)
ligand
are
crucial
to
successful
reaction.
